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Merck
CN

SML4211

Fluorosamine

≥98% (HPLC), (liquid to crytals), CSPG synthesis inhibitor

Synonym(s):

(3R,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)-5-fluorotetrahydro-2H-pyran-2,4-diyl diacetate, 2-Acetamido-4-fluoro-1,3,6-tri-o-acetyl-2,4-dideoxy-d-glucopyranose, peracetylated 4-F-GlcNAc, 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose, Ac-4-F-GlcNAc

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About This Item

Empirical Formula (Hill Notation):
C14H20FNO8
CAS Number:
Molecular Weight:
349.31
Assay:
≥98% (HPLC)
Form:
(liquid to crytals)
Quality level:
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Quality Level

assay

≥98% (HPLC)

form

(liquid to crytals)

color

white to yellow

storage temp.

2-8°C

General description

Fluorosamine is characterized by its fluorinated glucosamine structure, specifically modified at the 4-position with a fluorine atom. The presence of the fluorine atom is crucial for its inhibitory action on CSPG biosynthesis.

Application

Fluorosamine may be used in in vitro and in vivo models to study the mechanisms underlying remyelination and the role of extracellular matrix components in neural repair.

Biochem/physiol Actions

Fluorosamine (per-O-Acetylated-4-F-N-acetylglucosamine) is a cell-permeable inhibitor of chondroitin sulfate glycosaminoglycan (CS-GAG) chain assembly, reducing chondroitin sulfate proteoglycan (CSPG) activity and perineuronal nets (PNNs) in the arcuate nucleus (ARC). In vitro, at 10 µg/ml, Ac-4-F-GlcNAc significantly reduces neurofibrosis by preventing CS-GAG synthesis and elongation. In vivo, Fluorosamine administered intranasally (1 mg and 5 mg) or intracerebroventricularly (100 µg and 250 µg) depletes GanNAc, improves glycemic control, weight loss, and energy expenditure by restoring ARC insulin sensitivity in obese and diabetic mice. Additionally, it accelerates remyelination and exhibits immunomodulatory properties, reducing T-cell proliferation in CNS models.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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Global Trade Item Number

SKUGTIN
SML4211-5MG04065272931885
SML4211-25MG04065272931878

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